Proline L-脯氨酸

CAS 147-85-3 MFCD00064318

化学结构图

147-85-3
SMILES: O=C(O)[C@@H]1CCCN1

化学属性

Mol. FormulaC5H9NO2
Mol. Weight115.13
Density1.35
Melting Point228°C
TSCAYes
Solubility可溶
Appearance D 20 -85°(0.5-2.0 mg/ml,H2O),[α] -60.4°(0.5-2.0 mg/ml,5 mol/L HCl)。 powder 无色结晶,无臭,味甜;易溶于水(25℃水中溶解度为162.3 g/100 ml)和乙醇,不溶于丁醇及乙醚,遇水合茚三酮试液呈黄色,冰乙酸酸化后显红色;pI6.3,分解点为220-222℃;比旋光度[α]
Refractive index-85 ° (C=4, H2O)
Stability对光线敏感,对湿度敏感
Boiling Point252.2°C at 760 mmHg

别名和识别编码

Chemical NameL-(-)-Proline
CAS Number147-85-3
Alfabeta NamePROLINE L-
MDL NumberMFCD00064318
Synonym L-Proline {LY} L-Proline Proline {} {LY} L-Proline {} {} {LY} L-Proline {} {} {} {LY} L-Proline {} {} {} {} {LY} L-Proline {} {} {} {} {} {LY} L-Proline {} {} {} {} {} {} {LY} L-Proline {} {} {} {} {} {} {} {LY} L-Proline {} {} {} {} {} {} {} {} {LY} L-Proline {} {} {} {} {} {} {} {} {} {LY} L-Proline {} {} {} {} {} {} {} {} {} {} {LY} L-Proline {} {} {} {} {} {} {} {} {} {} {} {LY} L-Proline {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Proline {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Proline {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Proline {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Proline {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Proline {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Proline {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L
EC Number205-702-2
Beilstein Registry Number80810
PubChem Substance ID145742
Merck Number7780
Reaxys-RN80810
Chemical Name TranslationL-脯氨酸
LabNetwork Molecule IDLN00174821
Canonical SMILESO=C(O)[C@H]1NCCC1
InChIInChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1
信息真实价格透明    资金保障    专业采购外包团队在线服务   
信息真实价格透明    资金保障    专业采购外包团队在线服务   
品牌质保精细包装    现货库存    一流品牌服务   

分类

  • {SNA} Analytical Standards, Analytical
  • {SNA} Allium cepa (Onion), Allium sativum (Garlic), Aloe Vera, Amino Acids, Amino Acids & Vitamins, Amino Acids and Vitamins, Amino acids, Analytical/Chromatography, Biochemicals and Reagents, Cell Biology, Cell Culture, Core Bioreagents, Functional Foods, Ginkgo biloba, Hordeum vulgare (Barley), Humulus lupulus (Hops), Hypericum perforatum (St John's wort), Life Science Reagents for Cell
  • {SNA} Allium cepa (Onion), Allium sativum (Garlic), Aloe Vera, Amino Acids, Amino Acids & Vitamins, Amino Acids an

相关文献及参考

  • The Li salt has been used as a catalyst for the Michael addition of dimethyl malonate to ɑß-unsaturated aldehydes: J. Chem. Soc., Chem. Commun., 1088 (1991).
  • Short: III/20a
  • For preparation from L-proline of the chiral hydrazone "SAMP", and enantioselective syntheses using the RAMP/ SAMP methodology, see: Org. Synth. Coll., 8, 26, 403 (1985).
  • For use as a catalyst in an asymmetric aldol cyclization, see: Org. Synth. Coll., 7, 363 (1990). For reaction scheme, see 2-Methyl­cyclopentane-1,3-dione, A13936. For use in a direct enantioselective crossed aldol reaction with aldehydes, see: J. Am. Chem. Soc., 124, 6798 (2002). For use as an organoctalyst in direct aldol reactions of ɑ-oxyaldehydes, as the first step in a two-step synthesis of carbohydrates, see: Angew. Chem. Int. Ed., 43, 2152 (2004). Mediates the enantioselective borane reduction of ketones to chiral alcohols with moderate to good ee: Monatsh. Chem., 131, 91 (2000). Also used to induce high ee in the ɑ-amination of aldehydes with Dibenzyl­ azodicarboxyl­ate, L19347: J. Am. Chem. Soc., 124, 5656 (2002), or Diethyl­ azodicarboxyl­ate, L19348: Angew. Chem. Int. Ed., 41, 1790 (2002).
  • Short: III/5a
  • Merck:14,7780
  • For formation of a fused pyrrolidino-oxazolidinone, and use of the product in a synthesis of enantiopure ɑ-branched amino acids, see: Org. Synth. Coll., 9, 626 (1998); for reaction scheme, see Trimethyl­acetaldehyde, A15013.
  • Merck:14,7780 Beilstein:22,2
  • Short: II/2
  • For a review of the use of proline as a chiral catalyst, see: Synlett, 1675 (2001); Synlett, 1973 (2006).

安全信息

Warnings IRRITANT
Signal word Warning
GHS Symbol
WGK Germany1
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛,皮肤或衣服。
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
RTECSTW3584000
Storage condition RT, protect from light, stored under nitrogen {LY} RT, protect from light, stored under nitrogen Store at RT. {} {LY} RT, protect from light, stored under nitrogen {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} { {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {LY} RT, protect from light, stored under
Hazard Codes Xi
TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 10 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 372,75,1996

Hazard statements
UN Number
Packing Group

其他信息

  • {Chemicalbo
  • L-脯氨酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 62019933 L-脯氨酸 10g 22元 2011/04/16 P0481 L-脯氨酸 L-Proline 250G 2400元 2011/04/16 P0481 L-脯氨酸 L-Proline 25G 447元
  • 使用限量:占食品中总蛋白质量的4.2%(FDA,§172.320,2000) FEMA:同“01029,盐酸硫胺”。
  • 所属类别一:生物化学品: 氨基酸类: 中性氨基酸
  • {Chem
  • 所属类别三:生物化学品: 生化试剂: 氨基酸及其衍生物
  • 参考质量标准一:FCC,1996 含量(干燥后) 98.5%~101.5% 重金属(以Pb计,GT-16-2) ≤0.002% 铅(GT-18) ≤10mg/kg 干燥失重(105℃,3h) ≤0.3% 灼烧残渣(GT-27) ≤0.1% 比旋光度[α] D 20 (干燥试样4g/100ml 水) -84.0°~-86.3°
  • F:3-10
  • MSDS 信息:2-Pyrrolidinecarboxylic acid(147-85-3).msds
  • 参考质量标准二:原料药 中国药典2000年版772页 指标名称 指标 指标名称 指标 C5H9NO2含量/% ≥98.50/硫酸盐/% ≤0.03 比旋度 -83.7°--85.7° 砷盐
  • MOL 文件:147-85-3.mol
  • 方法三:L-脯氨酸有两种制法。 一是直接发酵法, 利用葡萄糖和黄色短杆菌变异株或谷氨酸棒杆菌野生株, 经微生物发酵获得L-脯氨酸; 二是化学合成法,以谷氨酸为原料, 与无水乙醇在硫酸催化下发生酯化, 并加入三乙醇胺将氨基硫酸盐游离出来, 得谷氨酸-δ-乙酯。 再用金属还原剂硼氢化钾还原谷氨酸-δ-乙酯, 得脯氨酸粗品, 最后对其分离纯化可得粗制脯氨酸。 小试工艺 酯化 称取L-谷氨酸147g, 投入三颈瓶中, 加入无水乙醇1L, 搅拌冷却至0℃, 再滴加H2SO4 80ml, 于0-5℃搅拌反应1h, 室温继续反应1h, 反应全部变清。 在20℃下滴加三乙胺至pH为8-8.5, 析出白色结晶, 在室温下再搅拌1h, 静置冷却5℃过滤, 取结晶, 用95%乙醇洗涤, 抽干后真空干燥,得谷氨酸-δ-乙酯约141g。熔点178-180℃, 收率80%-83%。 [α] 32 D +29.8 (C=1g/ml 10% HCl)。 还原 在三颈瓶中投入谷氨酸-δ-乙酯175g, 加入蒸馏水875ml, 搅拌冷却至5℃, 再分次加入KBH4 53.9g, 约1h加完, 室温再反应1h, 保温50℃反应3h。 冷却至0℃, 加入6mol/L HCl调至pH4, 过滤取滤液, 即得粗品L-脯氨酸水溶液。 分离纯化 离子交换树脂-氧化铝柱色谱分离法 将粗品L-脯氨酸水溶液, 以4ml/min的流速进入装入732-H + 型树脂交换柱中(1g 酸投料需10ml树脂)。 先用蒸馏水冲洗至中性,再用1mol/L氨水洗脱, 收集含L-脯氨酸段的洗脱液(用硅胶G薄层色谱控制)。 将洗脱液减压浓缩至干, 再用少量水溶解后,将其进入中性氧化铝色谱柱中,再以60%乙醇水溶液洗脱(还是用硅胶G薄层色谱控制)。 收集的洗脱液减压浓缩至干, 再以无水乙醇洗涤数次, 稍冷后再加入无水乙醚,冷却过滤取结晶, 真空干燥, 得L-脯氨酸。熔点220-222℃(分解),收率28%左右。 [α] 24 D -82.4 (C=1g/ml, H2O)。 五氯酚沉淀解吸分离法 成盐 将粗品制脯氨酸水溶液置于反应瓶中, 加热至50℃时滴加五氯酚乙醇溶液 (0.111mol/70ml乙醇), 并保温搅拌5h后, 让冷却至0℃, 过滤取结晶, 用少量冰水洗涤, 抽干, 干燥后得复盐, 熔点240-242℃, 沉淀率95%。 解析 将复盐38.4g, 投入三颈瓶中, 加入蒸馏水200ml, 氨水20ml, 室温搅拌8h, 冷却至0℃后过滤取滤液,将滤液减压浓缩, 加入蒸馏水100ml, 过滤取滤液, 加入
  • 参考质量标准三:含量大于99.5%,比旋光度[α] 20 D -81°-85°,氯化物(以Cl计)含量小于0.05%,硫酸盐(以SO 2- 4 计)含量小于0.05%,重金属(以Pb计)含量小于0.002

系列性分类